Evidence from several studies suggests it is impossible to engage in riskless judgment and decision-making (JDM). The purpose of this research study was to confirm these findings and delve into the influence of personality on risk propensity within JDM. The first hypothesis this research project explored supposed that extroversion and openness to experience, measured by the Big Five Inventory (BFI), would be positively correlated with elevated risky propensity, measured with the Factorial Objective Risk Test (FORT), the Risk Taking Inventory (RTI), and the Risk Orientations Questionnaire: Attitudes Towards Risk Decisions (ROQ). The subsequent hypothesis built upon the first and supposed neuroticism and conscientiousness would be negatively correlated with elevated risk propensity. The third hypothesis was that neuroticism and conscientiousness would be positively correlated with risk avoidance in JDM, measured with the ROQ. The fourth hypothesis was that risk attitudes, would be positively correlated with risk propensity, measured with the Factorial Objective Risk Test (FORT) and the Risk Taking Inventory (RTI). And the final hypothesis was that responses on the RTI, which measured the frequency of overall risk-taking in the six domains of recreation, health, career, finance, safety, and social, would be significantly correlated.